Winchester Condos for Sale

Welcome to Winchester, Massachusetts – a charming town that beautifully blends historic charm with modern convenience. Nestled in Middlesex County, Winchester is renowned for its picturesque landscapes, vibrant community spirit, and excellent educational institutions. With a rich history dating back to the 17th century, the town boasts a variety of architectural styles, from colonial homes to contemporary designs, making it a delightful place to call home.

Winchester is celebrated for its lush parks, scenic walking trails, and an inviting downtown area filled with boutique shops, cafes, and restaurants. Residents enjoy a strong sense of community, with numerous events and activities held throughout the year, fostering connections among neighbors and families. The town's proximity to Boston allows for easy access to the city’s cultural and professional opportunities while providing a serene suburban lifestyle.

For those considering a move to this idyllic town, there are a variety of condos for sale that cater to different lifestyles and budgets. Whether you’re seeking a cozy one-bedroom unit or a spacious multi-bedroom condo, Winchester's real estate market offers something for everyone. Many of these condos feature modern amenities, open floor plans, and stunning views, perfect for both first-time buyers and those looking to downsize.

Living in Winchester means embracing a lifestyle of convenience, community, and charm. Explore the available condos today and discover your new home in this enchanting town where history meets modern living!

Newest Winchester Condos for Sale

$700,000

2 Beds ⋅ 2 Baths ⋅ 73581469 MLS ⋅ ['Wedgewood Place'] BLDG.

Easy one-floor living in Winchester Center with garage parking for one car! Fabulous location near town center, TRAIN, shopping, restaurants, schools and library. Enjoy the open layout with extra wall of beautiful kitchen cabinets, large peninsula/eating bar, fireplace, balcony and a nook for a desk or whatever you wish. Large primary bedroom has two windows, large walk-in closet and full bath. Second bedroom is across hall from laundry and bath with shower. Air handler and condenser replaced in 2022. Central air throughout. Hot water heater and water shutoff installed - 2018. The additional storage unit is off the main lobby for easy access. Amenities include 2 elevators, inviting POOL and onsite rubbish pickup. Perfect home for first time buyers, downsizers, anyone commuting to Boston or in search of a vibrant town center lifestyle. New budget meets conventional financing guidelines!

666 Main Street Unit 217, Winchester

Listing courtesy of Listing Agent: Elizabeth Darby from Listing Office: Berkshire Hathaway HomeServices Commonwealth Real Estate.

$1,295,000

3 Beds ⋅ 3 Baths ⋅ 73580454 MLS ⋅ ['The Ledges'] BLDG.

This Ledges "A" Style townhouse condo offers extensive single floor living with a spacious first floor primary suite as well as a separate second floor suite and loft area. The main bedroom is truly vast. The first floor den can be used as a third bedroom. The home is move-in ready with all new oak hardwood floors throughout the finished areas! Entirely freshly painted in Moore's attractive Simply White. With cathedral ceilings, tall sunny windows, exterior deck, living room with fireplace, formal dining room, den/3rd bedroom, and kitchen with breakfast area, the home offers a lovely balance of airy open living and generous private spaces. Only bathrooms and kitchen are tiled. The home is located on a private cul-de-sac, with attached two-car garage offering convenient safety in snowy and icy weather! Enormous walk-out basement with high ceilings should you wish to expand your domain! Except for the front garden, all landscaping, exterior maintenance, snow removal done for you while you enjoy the association clubhouse, outdoor pool, tennis court and walking trails in the adjacent Sucker Brook Conservation area. Just minutes from Boston via car or train from charming Winchester Center with its coffee shops, restaurants and outdoor summer dining, pharmacies, and Whole Foods Market all near.

7 Wainwright Rd. Unit #47, Winchester

Listing courtesy of Listing Agent: Felicity F. Tuttle from Listing Office: Better Homes and Gardens Real Estate - The Shanahan Group.

$319,000

1 Beds ⋅ 1 Baths ⋅ 73580409 MLS ⋅ ['Parkview'] BLDG.

Best Price 1 Bedroom at The Parkview in Winchester! An exceptional opportunity to own in Winchester at an accessible price point! This first-floor, one-bedroom Terrace level at The Parkview offers an unbeatable combination of convenience, affordability, and practical living. Positioned on the ground level for easy direct access, the unit features peaceful views of the scenic duck ponds and mature, green landscaping. Step inside to an efficient open-concept layout where the kitchen features a functional peninsula and brand-new, never-used stainless steel appliances. All inclusive monthly HOA fee. Perfect for budget-conscious buyers, investors, or downsizers, completely covers your major monthly utility expenses: heat, hot water, electricity, water/sewer, and central air conditioning. In an era of rising utility costs, this structure provides total peace of mind and simplified monthly budgeting. Residents also enjoy access to the community pool, outdoor picnic grounds, and ample open parking. The location provides premium convenience, situated just minutes from vibrant Winchester Center with its local shops, cafes, highly rated restaurants, and two MBTA commuter rail stations for a straightforward commute. Enjoy everything Winchester has to offer, from the acclaimed public school system to the nearby trails of the Middlesex Fells Reservation, alongside quick access to Route 3 and I-93. If you have been searching for a smart entry into a high-demand market or a turn-key rental property with highly predictable expenses, this unit delivers outstanding utility and location for the price. ~DIRECTIONS TO UNIT~ park in lot to the right and walk to the rear of the building (the part with the duck ponds) it is a terrace level with its own door unit T-14

200 Swanton St Unit T14, Winchester

Listing courtesy of Listing Agent: The Synergy Group from Listing Office: The Synergy Group.

$399,000

1 Beds ⋅ 1 Baths ⋅ 73579389 MLS ⋅ ['Parkview Condominiums'] BLDG.

Welcome to Parkview Condominiums in Winchester! This well-maintained 1-bedroom, 1-bathroom condo offers comfortable living in a desirable location. The spacious living room features a glass slider that opens to a private balcony overlooking the pond and garden, perfect for relaxing and enjoying the peaceful surroundings. The condo fee includes all utilities, including heat, hot water, and electricity, as well as access to the in-ground swimming pool. A private basement storage unit is also included for added convenience. With its comfortable layout, private balcony, pond and garden views, included utilities, and convenient location, this move-in-ready condo is a great opportunity you won’t want to miss!

200 Swanton St Unit 727, Winchester

Listing courtesy of Listing Agent: Alice Zheng from Listing Office: Shore Real Estate LLC.

$495,000

2 Beds ⋅ 1 Baths ⋅ 73578112 MLS ⋅ ['Parkview'] BLDG.

Enjoy the best of Winchester living in this beautifully updated two-bedroom condo at Parkview, just minutes from Winchester Center, local shops, dining, parks, and commuter access. A bright, open-concept layout creates an inviting flow for everyday living and entertaining. The modern kitchen features stainless steel appliances, while fresh paint throughout adds a crisp, contemporary feel. Both generously sized bedrooms offer excellent closet space and flexible living options. The living area overlooks a scenic duck pond and professionally maintained grounds, creating a peaceful setting year-round. The secure card-entry building offers ample resident parking, guest parking off Swanton Street, and access to an in-ground pool. HOA includes heat, hot water, electricity, and AC for exceptional convenience and value. One basement storage unit is included.

200 Swanton St Unit 303, Winchester

Listing courtesy of Listing Agent: Joseph Pollack from Listing Office: Redfin Corp..

$1,495,000

4 Beds ⋅ 3 Baths ⋅ 73577640 MLS

Move-in-ready luxury townhouse in Winchester with the space, privacy, and single-family-home feel rarely found in condominium living. Built in 2005 and thoughtfully updated, 7 Sherman Place is set on a cul-de-sac and offers 3,095 square feet across four finished levels with four bedrooms, two-and-a-half baths, a private one-car garage, and outstanding indoor and outdoor living spaces.The bright, open-concept main level features high ceilings, oversized windows, hardwood floors, upgraded lighting, fresh paint, and a gas fireplace. Designed for everyday living and entertaining, the living and dining areas flow into a chef’s kitchen with granite countertops, abundant storage, brand-new stainless-steel appliances, and gas cooking. Doors from the dining area open directly to a spacious private deck for outdoor dining and relaxation.The professionally designed, irrigated private yard is a standout feature for a Winchester townhouse. A pergola, distinct sitting and dining areas, curated landscaping, and a dedicated Zen garden create an inviting outdoor retreat for entertaining, gardening, or unwinding.The showstopping primary suite is one of the home’s defining spaces, featuring upgraded closet built-ins, a private balcony, and a fully remodeled spa-like bathroom with a deep soaking tub, custom glass-enclosed walk-in shower, and high-end finishes. Additional bedrooms and a renovated full bath provide comfortable, flexible living space. The finished lower level has been updated with handsome paneling, recessed lighting, and new flooring—ideal for a home office, gym, media room, or flexible bonus space. Direct garage access adds everyday convenience.Major updates include a four-zone Bosch HVAC system installed in 2024, central air conditioning, smart thermostats, renovated bathrooms, new kitchen appliances, a smart security-camera system, and fresh exterior paint. With its four-level layout, private garage, deck, balcony, and professionally landscaped yard, this home lives far more like a single-family residence than a traditional condo.Located approximately eight miles north of Boston, Winchester ranked No. 11 among 141 Greater Boston communities in Boston Magazine’s 2026 Top Places to Live analysis. Enjoy convenient access to Winchester Center, two MBTA commuter rail stations with direct Lowell Line service to North Station, I-93, I-95, Cambridge, downtown Boston, and the Middlesex Fells Reservation.

7 Sherman Place Unit 7, Winchester

Listing courtesy of Listing Agent: John Dean from Listing Office: Engel & Volkers Boston.

$775,000

3 Beds ⋅ 2 Baths ⋅ 73575116 MLS

Carefree professionally managed condo convenience in Winchester Center! Soaring ceilings and generous living spaces make this home feel exceptionally spacious and inviting. Plenty of space to gather in the bright living room with oversized windows, family room with beautiful french doors, and large dining room with new built-in bar area. A versatile bonus room is perfect for a home office, gym, or additional living space. The kitchen opens directly to the generous dining room and features granite countertops, stainless steel appliances, and access to the deck. A full bathroom completes the first level. Upstairs, you’ll find three bedrooms, another full bathroom, and convenient laundry. This spacious home also offers a shared fenced-in yard, off-street parking for two cars, and additional storage in the basement. Abundant public transportation plus the charming shops and restaurants of Winchester Center, as well as elementary, middle, and high schools all at your fingertips. Welcome home to Winchester!

189 Washington St Unit 2, Winchester

Listing courtesy of Listing Agent: Kim Covino & Co. Team from Listing Office: Compass.

465 Washington Street Unit 465, Winchester

$1,300,000

4 Beds ⋅ 3 Baths ⋅ 73574929 MLS

Refined, low-maintenance living with the scale, finishes, and lifestyle advantages rarely found at this price point. This 4-bedroom, 3-bath townhouse (built in 2017) features open-concept design and high-end finishes. The main living area is anchored by a designer chef’s kitchen with premium appliances and a large island that flows to a large living room with a gas fireplace. The primary suite is a true oasis with a walk-in closet, spa bath, and a private balcony for evening relaxation. 3 other bedrooms, a refined bath plus second floor laundry provide flexibility for family, guests, or home office needs. The lower level is versatile, perfect for a media room and home gym. Convenience & Amenities: Enjoy a private, fenced backyard, dining patio, EV charger, and premium parking. Quick access to the Fells, major routes, plus close to top schools, parks, and the town center for an easy downtown commute. A rare turn-key value, bigger and better than most single families at this price.

465 Washington Street Unit 465, Winchester

Listing courtesy of Listing Agent: The Pallotta Group from Listing Office: Gibson Sotheby's International Realty.

$660,000

2 Beds ⋅ 2 Baths ⋅ 73572854 MLS

Enjoy Winchester living in this spacious 2-bed, 1.5-bath townhouse at the desirable Wedge Pond Condominium. The main level features hardwood floors, a sunny living room, dining room, half bath, and kitchen. On the second level, you have two bedrooms and a full bath. The finished lower level offers more space for a family room, home office, or guest bedroom, plus laundry and storage. To top it all off, you have a private outdoor patio with water views! One deeded parking space included with an additional second space available for $40 per month. Prime location - walk to downtown restaurants, commuter rail, schools, supermarket, beach, and much more. Updates include kitchen (2020) downstairs bathroom (2023) new windows (2026) heating (2020)

60 Lake St Unit E, Winchester

Listing courtesy of Listing Agent: Shaundize Moosavizadeh from Listing Office: Coldwell Banker Realty - Boston.

$1,999,000

4 Beds ⋅ 4 Baths ⋅ 73556476 MLS ⋅ ['The Ledges'] BLDG.

Experience elevated living in this exquisitely renovated luxury townhouse at The Ledges! This sought-after condominium community, just minutes from Winchester Center, offers the ease of low-maintenance living w/ the feel of a single-family home, plus exceptional amenities including a private clubhouse, swimming pool, & tennis courts. Featuring the community's most desirable floor plan, this home offers an elegant first-floor primary suite w/ dual walk-in closets and a stunning spa-inspired bath. Meticulously reimagined from top to bottom, every element of this extraordinary renovation was thoughtfully curated using the finest imported designer finishes and bespoke craftsmanship, creating an unparalleled level of luxury. The dramatic open-concept main level is highlighted by soaring vaulted ceilings, a fireplaced living room w/ a custom-designed mantel, & walls of glass that open to a private deck overlooking breathtaking western sunsets & tranquil natural surroundings. The designer kitchen is a true showpiece, featuring premium finishes, a sun-filled breakfast area, & seamless flow into the elegant dining room, ideal for both intimate gatherings & entertaining.The second floor offers 3 rooms including a spacious bedroom, beautifully renovated full bath, loft ideal for a home office, & an additional sitting room/TV room or guest space. The walk-out lower level it’s another suite in itself offering a spacious family room, second kitchenette, dining area, game room, additional bedroom with double closets, a luxurious spa bath, oversized laundry room, and abundant storage. Step outside to a private patio surrounded by peaceful, picturesque grounds, creating the perfect retreat for relaxing or entertaining. Ideally located w/ easy access to Winchester Center, Whole Foods, major highways, restaurants, and shops, this exceptional home offers luxury living just 7 miles from downtown Boston.

7 Wainwright Road Unit 113, Winchester

Listing courtesy of Listing Agent: Kim Covino & Co. Team from Listing Office: Compass.

$685,000

2 Beds ⋅ 2 Baths ⋅ 73553517 MLS ⋅ ['Wedgewood Place'] BLDG.

Inviting open layout with abundant natural light coming through NEW TRIPLE-PANE WINDOWS and NEW SLIDER (2026) for improved energy efficiency and beauty. Kitchen features updated appliances, granite counters with an eating bar and pantry closet; open to living room with fireplace and dining room with new chandelier. Spacious primary bedroom has LARGE WALK-IN CLOSET plus a sink and linen closet before the entry to the water closet where you'll find a large tub. Second bedroom/office has double closet and is across hall from IN-UNIT LAUNDRY and SECOND BATH with shower. Throughout, enjoy CENTRAL AIR and find NEW LIGHT FIXTURES, FRESH PAINT THROUGHOUT, NEW VINYL "WOOD" FLOORING (all recently done in 2026), NEW WASHER AND DRYER 2025 and NEW HOT WATER HEATER (2024). Love the COVERED PARKING in the garage below the building, association POOL, two ELEVATORS plus the convenience of being only one flight of stairs up from the street level. Location near town center, TRAIN, shopping, restaurants, schools and library is superb. Great layout, garage parking, ideal location and numerous recent improvements make this a wonderful opportunity! New budget meets conventional financing guidelines!

666 Main Street Unit 211, Winchester

Listing courtesy of Listing Agent: Elizabeth Darby from Listing Office: Berkshire Hathaway HomeServices Commonwealth Real Estate.

$610,000

3 Beds ⋅ 3 Baths ⋅ 73549877 MLS ⋅ ['Winchester Green'] BLDG.

Ideally located just minutes from vibrant downtown Winchester, this spacious condominium offers easy access to shopping, restaurants, the Farmer's Market, library, award-winning schools, parks, and the commuter rail. The renovated kitchen features custom maple cabinetry, granite countertops, a breakfast bar, and an open-concept layout that flows seamlessly into the living area—perfect for everyday living and entertaining. The second floor includes a full bath, a bedroom, and a versatile bonus room ideal for a home office, playroom, or guest space. The private third-floor primary suite features skylights, a custom-designed bath with a built-in makeup vanity, and generous storage. The finished lower level offers a family room, half bath, oversized closets, and an in-unit laundry area with additional storage. Enjoy easy access to the 2,600-acre Middlesex Fells Reservation, offering miles of scenic walking, running, and biking trails.

247 Washington St Unit 11, Winchester

Listing courtesy of Listing Agent: Heejeong Joo from Listing Office: Coldwell Banker Realty - Lexington.

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